The more things change, the more they stay the same. Hearing that phrase and seeing it in action are two different experiences. Hearing about historical quagmires makes them feel abstract and translucent, like a ghost, to the people not surrounded by them, but seeing those same problems up close makes them tangible struggles that are impossible to deny.

Of course, many things in the present don’t act as a carbon copy of the past, but seeing similarities between time periods in a world that we’re told moves quickly often becomes an exercise in anxiety.

When rapper Matt Monday came up with the idea to bring three generations of African-American musicians together, he wanted to explore the parallels and polarities between Charleston artists. Monday envisioned a conversation that showed “what it took to establish the foundation and what it takes to continue pushing the boundaries so the next generation can take it even further,” he says. The conversations that followed succeeded in that, but they also provided a history lesson that Monday won’t forget without a bout of amnesia.


Before things got rolling, Monday already had an understandable respect for the two jazz linchpins who he decided to interview, saxophonist Lonnie Hamilton III and trumpeter Charlton Singleton. And his deference to the artists deepened after the voice recorders were turned off. He met up with Hamilton first and immediately realized that the saxophone player would do most of the talking.

Giant Steps

As Monday tells Hamilton about the conversation he wants to have with him, he reminds Hamilton about a time they met before, not knowing if the jazz professional remembers it.

Monday produces a picture of himself in middle school with his grandmother and Hamilton at a play in honor of the saxophonist. As a student at School of the Arts, Monday performed in the play, which Charleston Jazz Orchestra Conductor and Artistic Director Charlton Singleton conducted. Monday explains to Hamilton that his grandmother was a huge fan of Hamilton’s student band at Bonds-Wilson High School, where she had attended classes. “Everyone in that pic influenced each other musically. My grandmother was influenced by Lonnie and his band at school,” says Monday. “I was influenced by her leading the choir in song on Sundays.”

Things came full circle before they even started.

Monday was captivated for all of Hamilton’s story, not saying a word aside from the occasional “wow,” because it’s hard not to hang onto every word of Hamilton’s narrative.

Like the best jazz artists, Hamilton was a staunch rebel to the form. His story is one of perseverance. But, unlike some of the most famous jazz musicians, he was an educator and an unlikely political figure in Charleston County, largely thanks to the love and cooperation he inspired in his music students, both black and white. And it all started with a saxophone under a Christmas tree.

In modern times, Hamilton is known as one of the Jenkins Orphanage’s most beloved sons. The Jenkins Orphanage was a home for abandoned children formed in the late 1800s by Reverend Daniel Jenkins. It was world-renowned for its band that took to the streets of Charleston (and eventually cities like Paris, Rome, London, and Berlin) to earn money for the orphanage. The band would become known as one of the earliest examples of jazz music in the Southeast.

The now-90-year-old Hamilton was born in 1927 and as a kid watched the famed jazz school’s Saturday afternoon parades. “They would go from Spring Street to Broad Street,” Hamilton recalls. “They would stop, periodically, to play for people.” Despite his untrained ear at the time, Hamilton loved the sounds he heard from the Jenkins Orphanage. “After following them from Spring Street down to Broad Street, you get to the place that you think, ‘Man, what it would be like to be with those guys,'” he says.

Hamilton wanted to join the orphanage band, despite the fact that he was not an orphan, nor did he have, as far as he knew, any musical abilities. The solution? He asked his grandfather for a saxophone for Christmas. “During those days, you didn’t have specialized people doing teaching and stuff like that. My original [saxophone] teacher was a trumpet player,” says Hamilton. His teacher, Holland Wrightson Daniels, educated young Hamilton on the basics of music theory. After studying saxophone more deeply, Hamilton joined the Jenkins Orphanage Band when a chair opened up. “I would walk on the street, and they would say, ‘Lonnie, would you hold up the music when they stop at Calhoun Street?'” he says. “That was one of the biggest thrills in the world.”

Hamilton grew as a musician, eventually performing in the Jenkins Orphanage traveling band. In fact, he grew so much as a musician that jazz bandleader Lionel Hampton scouted him and local bassist Leon Jones out for his band. “[Hampton] said, ‘I’m going to put you in my band,'” Hamilton says. “I’m 15, and I’m excited. I’m happy, and I ran home to my mama and I said, ‘Mama, I’m going on the road. I’m going to play with Lionel Hampton’s band.’ She said, ‘You’re going to college.'”

Hamilton’s mother made the right decision for her son, because soon after Hampton took Jones on the road, the young bass player was found naked and dead of an overdose.

The shock of hearing about his friend affirmed what his mother told him. And, although he did not have the money for higher education, Hamilton went to South Carolina State University on scholarship because of his musical abilities. The musician worked away in the dining hall to take care of his meals while also becoming the leader of one of the school’s dance bands. He graduated from S.C. State in 1951.


Hamilton did not begin his career as an educator until the mid-’50s at Sims High School in Union, S.C. His job was to create a music program for the school, and he was so successful that the principal of Bonds-Wilson High School asked him to start a music program in Charleston. With a measly $1,300 budget, Hamilton built a band for the segregated and impoverished school. “Due to the fact that it wasn’t integrated, you don’t get things,” observes Hamilton. “You’re the last people they think about.”

For the 20 years that the saxophonist worked at Bonds-Wilson, he worked with the meager conditions he was dealt and consistently trained young musicians who were in demand. “I had one of the top high school bands on the East Coast,” says Hamilton. “If I said to Sam Jones, who happened to be the band director at whatever university, that I had some kids that wanted to go to school that didn’t have the money — ‘Send them to me.’ They don’t even audition, they just send them.” Hamilton claims that in that time, he sent 131 kids to college who didn’t have a quarter. “All they had was the ability to play,” he says.

Bonds-Wilson students, even with their adroit musicality, had to prove themselves to secure their spot at local Christmas parades. “We didn’t have uniforms, because we never got the same kinds of treatment, being all black,” explains Hamilton. “We wore gray trousers and white shirts. That was our uniform, while all the white bands had uniforms.” Hamilton’s band, as he describes it, “turned the Christmas parade out.” After proving themselves in front of the major marching bands from the area, Hamilton demanded uniforms and, soon after, better instruments for his band. His band received both.

In 1970, 16 years after Brown v. Board of Education, integration came to Bonds-Wilson. “The school officials did not want me to stay as a teacher, because you didn’t do a lot of teaching white kids then,” says Hamilton. The highly qualified educator was offered a position as the vice principal. Thanks to his reputation as a music teacher, white students and their parents lobbied for Hamilton to stay where he was. “They went to the superintendent and told the superintendent that they wanted me to stay as a teacher of all kids,” he explains.

Hamilton became a surrogate father to some of his white and black students. One white young man named Foster told him that after his father had left his mother, Hamilton was the only example of a paternal relation that he had. “He knew no other father than me, and he was honored to have me as that father,” says Hamilton.

Years later, he even gave away one of his white students at her wedding at the University of South Carolina. “It frightened the hell out of me,” says Hamilton with tears in his eyes.

But he’d later experience further rejection in the school system. “When I got out of college, the University of South Carolina turned me down [for a master’s degree], because I was black. They told me they would give me money to go someplace else.” In response, he headed off to VanderCook College of Music in Chicago, Ill. USC attempted to strong-arm him into attending their school for the last semester of his master’s degree because they finally admitted African-American students. Hamilton said, “Like hell,” and threatened to sue them if they took away the funds they provided for him to study at another school. He says USC peacefully let him finish his studies out of state.


During his time as an educator, Hamilton was on the Charleston County Council. It was the beginning of a political career that brought him to a successful bid for a seat in Charleston County Council with the intent to help kids from Bonds-Wilson who wanted an African-American representative to better their environment. But before his campaign began, the school board he worked for told Hamilton that he could lose his job if he ran. Out of fear of being fired, Hamilton decided not to run for office until lawyer Gedney Howe got involved and informed Hamilton that the school board was infringing on his civil rights. “They backed off, and that allowed me to go on,” says Hamilton.

The educator’s leap into politics was thanks to his students. Both black and white students, with their parents’ knowledge, began phoning everyone they could to encourage folks to vote for Hamilton. “I was running against two white guys,” recalls Hamilton. “When the election was held, that night, I was leading by I think 200 votes. They said, ‘Lonnie, you can’t win this election because there’s only one box to come in, now, and that box is Isle of Palms. All white, only a couple of black people over there, and the white people aren’t going to vote for you.’ When Isle of Palms’ box came in, I won. Why? Because my white kids went out there and blasted them.”

“It’s almost like you were a part of the integration, yourself,” says Monday. Hamilton agrees.

“I had not trouble with color,” says Hamilton. “I saw my kids as my children, and they saw me as Daddy.”

“How much change can you say you personally think there has been from being born in ’27,” Monday asks.

“Matt, as I see it, the more things change, the more they remain the same,” Hamilton responds. “Psychologically, we’re still slaves because for a long time, they fed us that we had to depend on [slave] masters to live. And that will be with you. That is with you for a long time. And some of us are still out there and don’t understand where to go, and that will be with us for generations.”

Miles Ahead

Hamilton may show concern for the mentality of the black community in the future, but his effects on the local music scene are tangible. He stood his ground through every storm America threw at him, directly paving the way for a new generation of musicians and artists, like Charlton Singleton. “Lonnie was the last band director for the Jenkins Orphanage, and that means something,” says Singleton, reflecting on Hamilton’s legacy.

The parallels that Singleton’s story has with Hamilton’s are palpable. In so many ways, Singleton needs no introduction. The trumpeter is a seasoned performer in the jazz scene, one-fifth of Billboard-ranked Gullah band Ranky Tanky and the conductor and artistic director of the Charleston Jazz Orchestra.

The trumpet virtuoso came of age in the ’80s and ’90s, switching instruments a couple times before landing on the one that would take him everywhere. “I grew up going to church every Sunday,” says Singleton. “Just me listening to [the church organists] and trying to emulate what they were doing on the keyboard was probably the earliest influences that I had.”


Although Singleton says he didn’t get into jazz until college, where he “kind of was forced into it,” he was a frequent guest of Henry’s on Market Street, the jazz club that Hamilton often performed at. “Lonnie would have me come around and just listen to his band play,” says Singleton. When he finished college, Singleton sat in with Hamilton’s band a handful of times. Despite having a deep respect for Hamilton, Singleton believes that his biggest influence is church.

As Singleton and Monday continued their interview, Monday realized a parallel between Hamilton and Singleton. “You were the first African-American bandleader at SOA [Charleston School of the Arts],” observes Monday. “He [Hamilton] was the first at Bonds-Wilson, which was before it was integrated, but he was the first teacher to take that program to where it was, and I want to say you were the first African-American teacher at my high school to take that program to another level.”


Singleton says that the SOA band was already well put together by the time he got there, but is proud of the accomplishments he reached in his tenure. “Being in that position at arguably what is supposed to be the highest artistic school in the county — yeah, that was a good feeling,” says Singleton.

When contemplating the state of the Charleston music scene in the past and present, Singleton believes that more people are getting involved in jazz music, but also says, “We still have a long long way to go in terms of getting people to understand just how ridiculously talented Charleston musicians are.”

His biggest gripe with the modern jazz scene, and one that parallels Monday’s experiences in the local rap world, is the lack of dedicated jazz clubs. “There are restaurants that play all kinds of music, but they’re restaurants first,” says Singleton. “There’s not a place where you can go and it’s catered to listening to jazz. One of my pet peeves is that I’ll go and I’ll play in a restaurant and they’ll ask me to play quietly like it’s background music. Sometimes, I’m like, ‘Why not just put on the radio, why not just put on the T.V., why not just put on Pandora or something like that?'”

Where Hamilton inspired Singleton, Singleton inspired Monday. “I had just come from a predominately black school — nothing but black teachers, black students,” Monday tells Singleton. “Coming to [SOA], it wasn’t a culture shock, but it was completely different. And then, to see you come in as an African-American, teaching, composing — it was extremely inspiring.”


As segregation was an inescapable force in most of Hamilton’s youth, Monday asked Singleton what it means to him to be able to perform at large venues like the Gaillard and pull a large crowd from all walks of life. “I definitely would not be performing in those places if not for people like him [Hamilton],” says Singleton. “I’ll always be proud of the hard work and the accomplishments that I’ve been able to do, but all of those are based off of piggybacking off of folks like Lonnie Hamilton.”

When Singleton became the first artist in residence at the new Gaillard Center, and the first African-American artist in residence in the Gaillard’s 50-year history, jazz artists began calling him to congratulate him. “It took me a while for it to sink in,” says Singleton. “Folks like Lonnie called me up and they were just like, ‘Congratulations, this is such a big honor,’ and I’m like, ‘It’s just a job.'” According to Singleton, Hamilton told him, “No, this is a little bigger than that, young blood.” He still holds his position as artist in residence at the Gaillard.

Although Singleton is no longer a full-time educator, he still loves going to schools and speaking to kids in the hopes of inspiring students to get involved in music.

Which brings us to the present. Both Singleton and Hamilton are active participants in the jazz scene, but their legacy paved the way for other African-American artists like rapper Matt Monday.

Tomorrow is the Question

The day after his interview with Lonnie and a few hours after his talk with Charlton, Monday contemplates everything he’s heard from the two Charleston icons in such a short amount of time.

The first topic to come up is Singleton’s observation that there are no dedicated jazz venues. “There are no hip-hop clubs here,” states Monday. “So, when I play the Music Hall or I get the Music Farm or Spoleto, I know how grateful I am.”

“To me, it was mind-blowing that they go in there and tell Charlton to be quiet,” Monday adds. Many rappers in the area have dealt with the same issue, often told to turn their music down or do radio edits. “There’s nowhere for these art forms to blossom to their full potential,” he says.


Monday has been an omnipresent force in the rap scene since the late ’00s, originally performing as Righchus. Just as Singleton, he was first introduced to music in church. Even in his early days, the budding rapper had a music video on BET and opened up for J. Cole and Bone-Thugs-N-Harmony. After the name change, Monday started his own label, SWIM, and he continues to release music that has earned him the City Paper‘s Best Hip-Hop Artist award a handful of times in the past 10 years.


In a parallel to Hamilton and Singleton, Monday is one of the Charleston rap scene’s biggest, and also one of the most outspoken about unfair treatment toward his genre. “I couldn’t name one genre or art form curated by black who that is allowed to fully blossom anywhere in Charleston, whether you’re talking about clubs, bars, or whatever,” says Monday. “Anything associated with us isn’t put on the forefront, and I feel like that’s not what they’re trying to market from us. They want [to market] the old slave culture.”

At almost every turn over the course of the two hours worth of interviews he partook in, Monday seemed incredibly humbled by the struggles, sacrifices, and progressive leaps the previous generations made. “I know what black musicians here have gone through for me to even say these things,” Monday says. “I’ve got to approach things a certain way to kind of uphold the prestigious legacy that Lonnie has started, that Charlton is continuing. And whether I want to or not, I’m a representation or extension of that, by just being a black musician or artist in this city.”


Maybe saying “the more things change, the more they stay that same” isn’t accurate in this case. Hamilton’s experiences in Charleston jazz music broke the dam, at times creating a true unity among white and black citizens, and Singleton pushed representation of black musicians one step further. Monday, and plenty of other artists like Benny Starr, Contour, and Jah Jr., continue to bring esteem to the local hip-hop scene and beyond. Some of those artists openly attempt to fight unfair treatment when they see it.

And let’s not be fooled — racism is still a fierce presence that haunts the city. If that dark force didn’t remain, Monday wouldn’t make observations about the inequality amongst the collective music scenes of the Holy City. But, the fact that he can say them out loud and people will listen, highlights that things have changed — and they haven’t stayed exactly the same.

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